Organic compounds and organic light emitting diodes comprising the same

Abstract

The present application provides a novel organic compound and an organic light emitting diode comprising the same. An organic light emitting diode of an embodiment of the present application includes a first electrode; a second electrode disposed opposite the first electrode; and one or more organic layers between the first electrode and the second electrode, at least one of the one or more organic layers comprising an organic compound represented by Chemical Formula A of the present application, thereby improving driving voltage, efficiency, and lifespan characteristics of the organic light emitting diode.

Description

Technical Field

[0001] This invention relates to an organic compound and an organic light-emitting diode comprising the same. Background Technology

[0002] Compared with other flat panel display devices such as liquid crystal displays (LCDs), plasma flat panel displays (PDPs), and field emission displays (FEDs), organic light-emitting diodes (OLEDs) have a simpler structure and several advantages in manufacturing processes. They also have excellent high brightness and viewing angle characteristics, fast response speed, and low driving voltage. Therefore, they are being actively developed for use as light sources for flat panel displays such as wall-mounted TVs, backlighting of displays, illumination, and billboards.

[0003] An organic light-emitting diode (OLED) consists of an organic layer between two electrodes. It works on the following principle: electrons and holes are injected into the light-emitting layer from the two electrodes respectively. Electrons and holes combine to generate excitons. When the generated excitons fall from the excited state to the ground state, light is produced.

[0004] Organic light-emitting diodes (OLEDs) may include at least one light-emitting layer. Typically, OLEDs with multiple light-emitting layers include multiple light-emitting layers that emit light with different peak wavelengths, thereby enabling the achievement of a specific color through a combination of light with different peak wavelengths.

[0005] Organic light-emitting diodes (OLEDs) can be categorized into front-emitting and back-emitting structures. Front-emitting devices utilize a reflective first electrode (anode) to emit light generated from the light-emitting layer towards a semi-transparent or transparent second electrode (cathode). Conversely, back-emitting devices utilize a reflective second electrode to emit light generated from the light-emitting layer towards a transparent first electrode, which is aligned with the direction of the driving thin-film transistor, and then reflect the light back to the second electrode.

[0006] Existing patent literature Patent documents Existing patent document 1: Korean Patent Publication No. 10-2022-0156258 Existing patent document 2: Korean Patent Publication No. 10-2024-0044902 Summary of the Invention The problem the invention aims to solve The purpose of this invention is to provide a novel organic compound and an organic light-emitting diode comprising the same.

[0007] In addition to the problems mentioned above, embodiments of the present invention can also be used to address other problems not specifically mentioned.

[0008] The purpose of this invention is not limited to the purpose described above. Other purposes and advantages of the invention not mentioned can be understood from the following description and will become clearer through the embodiments of the invention.

[0009] Furthermore, it is obvious that the objects and advantages of the present invention can be achieved by means and combinations thereof shown in the claims.

[0010] means for solving problems According to one embodiment of the present invention, an organic compound represented by the following chemical formula A can be provided. The definition of chemical formula A is the same as that set forth in this specification and the claims.

[0011] Chemical formula A

[0012] In the above chemical formula A, X above represents oxygen (O) or sulfur (S). The n1 and n2 mentioned above are integers from 0 to 5. The above n3 is an integer from 0 to 3. The above n4 is an integer from 0 to 2. The above n5 is an integer from 0 to 4. The L1 and L2 groups mentioned above may be the same or different from each other, and each is independently a single-bonded, substituted or unsubstituted aryl group with 6 to 30 carbon atoms. The Ar1 and Ar2 mentioned above may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or an unsubstituted heteroaryl group having 3 to 60 carbon atoms. The R1 to R5 mentioned above may be the same as or different from each other, and each independently is selected from one of the following groups: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 60 carbon atoms. When L1, L2, Ar1, Ar2 and R1 to R5 are substituted, the substituents are selected from one or more of the group consisting of deuterium, cyano, nitro, halogen, hydroxyl, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 30 carbon atoms, heteroaryl having 3 to 60 carbon atoms, alkylamino having 1 to 10 carbon atoms, arylamino having 6 to 30 carbon atoms, heteroarylamino having 1 to 30 carbon atoms, alkylsilyl having 1 to 10 carbon atoms, arylsilyl having 6 to 30 carbon atoms, alkoxy having 1 to 10 carbon atoms, aryloxy having 6 to 30 carbon atoms, alkylthio having 1 to 10 carbon atoms, and arylthio having 6 to 30 carbon atoms. When multiple substituents are present, each substituent may be the same or different from the others.

[0013] According to another embodiment of the present invention, an organic light-emitting diode (OLED) can be provided, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic layers located between the first electrode and the second electrode, wherein at least one of the organic layers contains an organic compound represented by the above chemical formula A.

[0014] Invention Effects The organic compound represented by chemical formula A of the present invention can achieve excellent hole transport characteristics.

[0015] Furthermore, one or more of the hole transport layer and hole transport auxiliary layer of the organic light-emitting diode of the present invention contain an organic compound represented by chemical formula A of the present invention, thereby improving the driving voltage, external quantum efficiency and lifetime characteristics of the organic light-emitting diode.

[0016] Furthermore, when the organic compound represented by chemical formula A of the present invention is used as a hole transport auxiliary layer material, it can have a suitable energy level as a hole transport auxiliary layer, which plays the role of transporting holes from the hole transport layer to the light-emitting layer and blocking electrons from the light-emitting layer.

[0017] Furthermore, the organic light-emitting diode of the present invention, as a hole transport layer and / or hole transport auxiliary layer comprising the organic compound represented by chemical formula A of the present invention, can achieve excellent color coordinates as targeted by the above-mentioned light-emitting layer even when combined with a light-emitting layer of any color.

[0018] The effects of this invention are not limited to those mentioned above; those skilled in the art will clearly understand other effects not mentioned through the entire description herein. The above-mentioned effects and additional effects will be described in detail below. Detailed Implementation

[0019] The foregoing objectives, features, and advantages are described in detail below, enabling those skilled in the art to readily implement the technical concepts of this invention.

[0020] In describing this invention, a detailed description of known techniques related to this invention will be omitted if it is determined that such a description may unnecessarily obscure the gist of the invention.

[0021] In this specification, when referring to structural elements such as “including,” “having,” “forming,” “configuring,” or “possessing,” additional parts may be added unless “only” is used. When a structural element is expressed in the singular, it includes the plural unless otherwise specified.

[0022] When interpreting structural elements in this specification, they are to be interpreted as including tolerance ranges, even if not explicitly described separately.

[0023] In this specification, the phrase "arbitrary structure is arranged on the upper (or lower) part" or "above (or below)" of a structural element means that the arbitrary structure is not only in contact with the upper (or lower) part of the structural element, but there may also be other structures between the structural element and the arbitrary structure arranged on (or below) the structural element.

[0024] The expressions “at least one of a, b and c” and “of a, b or c” in this specification may include “a alone”, “b alone”, “c alone”, “a and b”, “a and c”, “b and c”, or “a, b and c”.

[0025] The term "halogen group" as used in this specification includes fluorine, chlorine, bromine, and iodine.

[0026] As used in this specification, the term "alkyl" refers to both straight-chain alkyl and branched-chain alkyl. Unless otherwise stated, alkyl groups contain 1 to 30 carbon atoms and may include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl, hexyl, etc. Furthermore, alkyl groups may optionally be substituted.

[0027] As used in this specification, the term "cycloalkyl" refers to a cyclic alkyl group. Unless otherwise stated, a cycloalkyl group contains 3 to 20 carbon atoms and may include, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, etc. Furthermore, the cycloalkyl group may optionally be substituted.

[0028] As used in this specification, the term "alkenyl" refers to both straight-chain alkenyl and branched alkenyl groups having one or more carbon-carbon double bonds. Unless otherwise stated, alkenyl groups contain 2 to 30 carbon atoms and may include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, etc. Furthermore, alkenyl groups may optionally be substituted.

[0029] As used in this specification, the term "cycloalkenyl" refers to a cyclic alkenyl group. Unless otherwise stated, a cycloalkenyl group contains 3 to 20 carbon atoms, and furthermore, the cycloalkenyl group may optionally be substituted.

[0030] As used in this specification, the term "alkynyl" refers to both straight-chain alkynyl and branched-chain alkynyl groups having one or more carbon-carbon triple bonds. Unless otherwise stated, an alkynyl group contains 2 to 30 carbon atoms and may include, but is not limited to, ethynyl, 2-propynyl, etc. Furthermore, the alkynyl group may optionally be substituted.

[0031] As used in this specification, the term "cycloynyl" refers to a cyclic ynyl group. Unless otherwise stated, a cycloynyl group contains 3 to 20 carbon atoms, and furthermore, the cycloynyl group may optionally be substituted.

[0032] The terms “arylalkyl” or “arylalkyl” used in this specification are used interchangeably and refer to an alkyl group having an aromatic group as a substituent. Further, arylalkyl (arylalkyl) may optionally be substituted.

[0033] The terms "aryl" or "aromatic group" used in this specification have the same meaning, and aryl groups include monocyclic and polycyclic groups. Polycyclic groups may include "fused rings," which consist of two or more rings, where two adjacent rings share two carbon atoms. Furthermore, they may also include forms in which two or more rings are simply attached or fused together. Unless otherwise stated, aryl groups contain 6 to 30 carbon atoms and may include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthraceneyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, etc. Further, aryl groups may optionally be substituted.

[0034] The terms "heteroaryl" or "heteroaryl group" as used in this specification have the same meaning, and heteroaryl includes both monocyclic and polycyclic groups. Polycyclic groups may include "fused rings," which are two or more rings in which two adjacent rings share two carbon or heteroatoms. Furthermore, they may also include forms in which two or more rings are simply attached to or fused together. Unless otherwise stated, the heteroaryl group contains 3 to 60 carbon atoms. In this case, one or more carbon atoms in the ring are substituted by heteroatoms such as oxygen (O), nitrogen (N), sulfur (S), or selenium (Se), which may include, but are not limited to: 6-membered monocyclic rings, such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; polycyclic rings, such as phenthioxyl, indoleazinyl, indoleyl, purine, quinolinyl, isoquinolinyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, carbazolyl, phenylcarbazolyl, 9-phenylcarbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, etc. Furthermore, the heteroaryl group may be optionally substituted.

[0035] As used in this specification, the term "heterocyclic group" refers to a group in which one or more carbon atoms constituting an aryl, cycloalkyl, cycloalkenyl, cycloalkynyl, aralkyl, or arylamino group are substituted with heteroatoms such as oxygen (O), nitrogen (N), or sulfur (S). Referring to the above definition, this includes heteroaryl, heterocycloalkyl, heterocycloalkenyl, heterocycloalkynyl, heteroarylalkyl, and heteroarylamino groups. Furthermore, the heterocycle may be optionally substituted.

[0036] Unless otherwise stated, the term "carbon ring" as used in this specification may include "cycloalkyl", "cycloalkenyl", "cycloynyl" as alicyclic cyclic groups and "aryl (aromatic group)" as an aromatic cyclic group.

[0037] As used in this specification, the terms “heteroalkyl,” “heteroalkenyl,” “heteroynyl,” and “heteroarylalkyl” refer to the substitution of one or more carbon atoms in the carbon atom constituting the group by heteroatoms such as oxygen (O), nitrogen (N), and sulfur (S). Furthermore, heteroalkyl, heteroalkenyl, heteroynyl, and heteroarylalkyl may be optionally substituted.

[0038] As used in this specification, the terms "alkylamino", "arylalkylamino", "arylamino", and "heteroarylamino" refer to amino groups (or amino groups) that are substituted with the aforementioned alkyl, arylalkyl, aryl, or heteroaryl groups, and include primary (or amino), secondary (or amino), and tertiary (or amino) groups. Further, alkylamino, arylalkylamino, arylamino, and heteroarylamino groups may optionally be substituted.

[0039] The terms “alkylsilyl”, “arylsilyl”, “alkoxy”, “aryloxy”, “alkathio”, and “arylthio” used in this specification refer to alkylsilyl, oxy, and thio groups that are substituted with the aforementioned alkyl and aryl groups. Further, alkylsilyl, arylsilyl, alkoxy, aryloxy, alkathio, and arylthio groups may be optionally substituted.

[0040] As used in this specification, the terms "arylene," "arylalkylene," "heteroarylene," and "heteroarylalkylene" refer to the aforementioned aryl, aralkyl, heteroaryl, and heteroaryl groups, each of which is a divalent substituent further comprising one substituent. Furthermore, the arylene, arylalkylene, heteroaryl, and heteroarylalkylene groups may optionally be substituted.

[0041] As used in this specification, the term "substitution" means that the hydrogen (H) atom bonded to the carbon atom, nitrogen atom, etc. of the compound of the present invention is replaced by a substituent other than hydrogen. When multiple substituents are present, each substituent may be the same as or different from each other.

[0042] The substituents mentioned above can be independently selected from deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxyl, trimethylsilyl, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, alkenyl having 2 to 30 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, alkynyl having 2 to 30 carbon atoms, cycloalkynyl having 3 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, aralkyl having 7 to 30 carbon atoms, heteroaryl having 3 to 60 carbon atoms, and others having 4 to 60 carbon atoms. Among the following groups: heteroaryl groups, amino groups, alkylamino groups having 1 to 30 carbon atoms, aralkylamino groups having 7 to 30 carbon atoms, arylamino groups having 6 to 30 carbon atoms, heteroarylamino groups having 3 to 60 carbon atoms, silyl groups, alkylsilyl groups having 1 to 30 carbon atoms, arylsilyl groups having 6 to 30 carbon atoms, alkoxy groups having 1 to 30 carbon atoms, aryloxy groups having 6 to 30 carbon atoms, alkylthio groups having 1 to 30 carbon atoms, and arylthio groups having 6 to 30 carbon atoms.

[0043] Unless otherwise stated, each object and substituent defined in this specification may be the same or different.

[0044] In this specification, unless otherwise stated, all units are based on weight (wt). For example, when stated as "%", it is interpreted as weight percentage (wt%).

[0045] The organic compounds of the present invention and organic light-emitting diodes comprising the thereof will be described in detail below.

[0046] The organic compounds of the present invention can be represented by the following chemical formula A.

[0047] Chemical formula A

[0048] In the above chemical formula A, The X mentioned above is selected from oxygen (O) or sulfur (S). The n1 and n2 mentioned above are integers from 0 to 5. The above n3 is an integer from 0 to 3. The above n4 is an integer from 0 to 2. The above n5 is an integer from 0 to 4. The L1 and L2 groups mentioned above may be the same or different from each other, and each is independently a directly bonded, substituted, or unsubstituted aryl group with 6 to 30 carbon atoms. The Ar1 and Ar2 mentioned above may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms. The R1 to R5 mentioned above may be the same as or different from each other, and each independently is selected from one of the following groups consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 60 carbon atoms. When L1, L2, Ar1, Ar2 and R1 to R5 are substituted, the substituents may be selected from one or more of the group consisting of deuterium, cyano, nitro, halogen, hydroxyl, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 30 carbon atoms, heteroaryl having 3 to 60 carbon atoms, alkylamino having 1 to 10 carbon atoms, arylamino having 6 to 30 carbon atoms, heteroarylamino having 1 to 30 carbon atoms, alkylsilyl having 1 to 10 carbon atoms, arylsilyl having 6 to 30 carbon atoms, alkoxy having 1 to 10 carbon atoms, aryloxy having 6 to 30 carbon atoms, alkylthio having 1 to 10 carbon atoms, and arylthio having 6 to 30 carbon atoms. When multiple substituents are present, each substituent may be the same as or different from the others.

[0049] According to one embodiment of the present invention, the aforementioned Ar1 may be a substituted or unsubstituted aryl group having 6-30, 6-25, 6-15, 6-12, or 6-10 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3-60, 3-30, 3-18, 3-12, 3-9, 3-8, 3-7, 3-5, or 3-4 carbon atoms. For example, it may be a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted phenyl-naphthyl group, a substituted or unsubstituted phenyl-phenanthryl group, a substituted or unsubstituted phenyl-dibenzofuranyl group, or a substituted or unsubstituted phenyl-dibenzothiophene group.

[0050] According to one embodiment of the present invention, the aforementioned Ar1 may be a substituted or unsubstituted aryl group having 6-30, 6-25, 6-15, 6-12, or 6-10 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3-60, 3-30, 3-18, 3-12, 3-9, 3-8, 3-7, 3-5, or 3-4 carbon atoms. For example, it may be a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted phenyl-naphthyl group, a substituted or unsubstituted phenyl-phenanthryl group, a substituted or unsubstituted phenyl-dibenzofuranyl group, or a substituted or unsubstituted phenyl-dibenzothiophene group.

[0051] According to one embodiment of the present invention, the Ar2 mentioned above may be an aryl group having 6 to 30, 6 to 25, 6 to 15, 6 to 12 or 6 to 10 carbon atoms, or a heteroaryl group having 3 to 60, 3 to 30, 3 to 18, 3 to 12, 3 to 9, 3 to 8, 3 to 7, 3 to 5 or 3 to 4 carbon atoms, substituted or unsubstituted. For example, it can be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted phenyl-naphthyl, substituted or unsubstituted phenyl-phenanthyl, substituted or unsubstituted phenyl-dibenzofuranyl, substituted or unsubstituted phenyl-dibenzothiopheneyl.

[0052] According to one embodiment of the present invention, the Ar2 mentioned above may be an aryl group having 6-30, 6-25, 6-15, 6-12, or 6-10 carbon atoms, or a heteroaryl group having 3-60, 3-30, 3-18, 3-12, 3-9, 3-8, 3-7, 3-5, or 3-4 carbon atoms, substituted or unsubstituted. For example, it may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted phenyl-naphthyl group, a substituted or unsubstituted phenyl-phenanthryl group, a substituted or unsubstituted phenyl-dibenzofuranyl group, or a substituted or unsubstituted phenyl-dibenzothiophene group.

[0053] According to one embodiment of the present invention, L1 and L2 may be a single bond (direct bond) or one of the substituents represented by F1 to F3 below. In F1 to F3 below, * indicates a binding site.

[0054] According to one embodiment of the present invention, Dn in F1 to F3 below represents the number of deuteriums replaced in the structure, where n, representing the number of deuteriums, is an integer greater than or equal to 0.

[0055] According to one embodiment of the present invention, n in F1 to F3 below is an integer selected from 0 to 4.

[0056]

[0057] According to one embodiment of the present invention, the Ar1 described above can be one of the substituents represented by M1 to M48 below. In M1 to M48 below, * represents a binding site.

[0058] According to one embodiment of the present invention, Dn in M1 to M48 below represents the number of deuteriums replaced in the structure, where n, representing the number of deuteriums, is an integer greater than or equal to 0.

[0059] According to an embodiment of the present invention, n in M1 and M2 is an integer selected from 0 to 7, n in M3 is an integer selected from 0 to 9, n in M4 to M11 is an integer selected from 0 to 7, n in M12 to M17 is an integer selected from 0 to 11, n in M18 to M20 is an integer selected from 0 to 13, n in M21 to M44 is an integer selected from 0 to 11, and n in M45 to M48 is an integer selected from 0 to 7.

[0060]

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[0070]

[0071] According to one embodiment of the present invention, the Ar2 described above can be one of the substituents represented by A1 to A58 below. In A1 to A58 below, * indicates a binding site.

[0072] According to one embodiment of the present invention, Dn in A1 to A58 below represents the number of deuteriums replaced in the structure, where n, representing the number of deuteriums, is an integer greater than or equal to 0.

[0073] According to an embodiment of the present invention, n in A1 is an integer selected from 0 to 5, n in A2 to A4 is an integer selected from 0 to 9, n in A5 to A10 is an integer selected from 0 to 13, n in A11 and A12 is an integer selected from 0 to 7, n in A13 is an integer selected from 0 to 9, n in A14 to A25 is an integer selected from 0 to 7, n in A26 to A31 is an integer selected from 0 to 11, n in A32 to A34 is an integer selected from 0 to 13, and n in A35 to A58 is an integer selected from 0 to 11.

[0074]

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[0085] According to one embodiment of the present invention, R1 to R5 may be the same as or different from each other, and may each be hydrogen or deuterium independently.

[0086] According to one embodiment of the present invention, the compound represented by the chemical formula A is selected from the group consisting of, but not limited to, the following compounds.

[0087]

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[0090]

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[0142] The organic compound represented by chemical formula A of the present invention is characterized in that the 4-position of the dibenzofuran is replaced by an umbrella-shaped terphenyl group, and an amino group is contained at the 1-position. Because the organic compound represented by chemical formula A of the present invention has the characteristic structural form described above, it exhibits superior hole injection characteristics compared to compounds that do not satisfy the structure of chemical formula A. Therefore, when used as a hole transport layer and / or hole transport auxiliary layer in an organic light-emitting diode, it helps to ensure characteristics such as low drive voltage, high efficiency, and long lifetime when evaluating device performance.

[0143] That is, when the organic compound represented by chemical formula A of the present invention is used as a hole transport layer material, it exhibits excellent hole mobility characteristics, thereby increasing the efficiency and lifetime of the device. Furthermore, in one embodiment, when the organic compound represented by chemical formula A of the present invention is used as a hole transport auxiliary layer material, it has excellent hole mobility characteristics and also possesses suitable energy levels for a hole transport auxiliary layer. It functions to transport holes from the hole transport layer to the light-emitting layer and block electrons from the light-emitting layer, thus increasing the efficiency and lifetime of the device.

[0144] Furthermore, the organic compound represented by Formula A of the present invention has a triplet energy level (T1) within an appropriate range required for the hole transport layer and / or hole transport auxiliary layer, thus effectively suppressing the diffusion of triplet excitons generated in the emissive layer to the outside and improving luminous efficiency and device lifetime characteristics. In particular, when the triplet energy level of the compound used as the hole transport layer and / or hole transport auxiliary layer is too high, it may also exhibit a tendency for the HOMO level to be too deep, thus reducing hole transport characteristics and ultimately leading to a decrease in device performance (such as an increase in driving voltage). Conversely, when the triplet energy level is too low, it is impossible to prevent the diffusion of triplet excitons generated in the emissive layer, thereby reducing device efficiency. The organic compound represented by Formula A of the present invention can have a triplet energy level within an appropriate range, which ensures a balance between the binding effect of triplet excitons and charge transport characteristics.

[0145] Furthermore, when the organic compound represented by chemical formula A of the present invention is used as a hole transport layer and / or a hole transport auxiliary layer, it has low driving voltage, excellent current efficiency and lifetime characteristics, and excellent color performance.

[0146] More specifically, when the organic compound represented by Formula A of the present invention is used as a hole transport layer or hole transport auxiliary layer (e.g., as a hole transport auxiliary layer), the efficiency and lifetime of organic light-emitting diodes can be improved. In this case, unlike the organic compound represented by Formula A of the present invention, when it does not contain heteroaryl or fused polycyclic aryl groups, or when the 4-position of dibenzofuran is substituted with a triphenyl group and the 1-position is not substituted with an amino group, the deposition temperature required in the deposition process to form the hole transport layer or hole transport auxiliary layer may be too high. As a result, not only is the deposition process itself inefficient, but the high temperature conditions in the deposition process can also lead to a decrease in molecular thermal stability. Conversely, with the organic compound represented by Formula A of the present invention, the triphenyl and amino groups are substituted at specific sites in the dibenzofuran, and it contains heteroaryl or fused polycyclic aryl groups, thereby ensuring efficiency and excellent molecular thermal stability in the deposition process.

[0147] An organic light-emitting diode according to an embodiment of the present invention includes: a first electrode (anode); a second electrode (cathode) disposed in relation to the first electrode; and one or more organic layers located inside the first electrode and the second electrode, wherein at least one of the above-mentioned organic layers is a hole transport layer or a hole transport auxiliary layer comprising an organic compound represented by the above-mentioned chemical formula A.

[0148] The organic layer may include one or more of the following: Hole Injection Layer (HIL), Hole Transport Layer (HTL), Hole Transport Auxiliary Layer, Emitting Layer (EML), Electron Transport Auxiliary Layer, Electron Transport Layer (ETL), and Electron Injection Layer (EIL).

[0149] For example, an organic light-emitting diode can have a structure in which a first electrode, a hole injection layer (HIL), a hole transport layer (HTL), a hole transport auxiliary layer, an emissive layer (EML), an electron transport layer (ETL), an electron injection layer (EIL), and a second electrode are stacked sequentially.

[0150] In one embodiment of the present invention, the organic layer containing an organic compound represented by chemical formula A may be a hole transport layer (HTL) or a hole transport auxiliary layer.

[0151] The aforementioned organic layer or more may further include one or more selected from the group consisting of a hole injection layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.

[0152] The first electrode can be an anode, and the first electrode can contain transparent and highly conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), and zinc oxide (ZnO).

[0153] The second electrode can be a cathode, and it can contain materials such as lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). Furthermore, in the case of a light-emitting organic light-emitting diode, indium tin oxide (ITO) or indium zinc oxide (IZO) can be used to form a transparent, light-transmitting second electrode.

[0154] A capping layer (CPL) can be formed on the surface of the second electrode using a composition for forming the capping layer.

[0155] Furthermore, a protective film (encapsulation layer or protecting layer) may be provided on the cover layer to protect the organic light-emitting diode from the effects of moisture and oxygen. This protective film may be formed from a curable adhesive composition containing an inorganic hygroscopic agent.

[0156] There are no particular limitations on the aforementioned hole injection layer or hole transport layer compounds, and any compound can be used as long as it is commonly used as a hole injection layer or hole transport layer compound. Non-limiting examples of hole injection layer or hole transport layer compounds may include phthalocyanine derivatives, porphyrin derivatives, triarylamine derivatives, indobenzocarbazole derivatives, etc. For example, 1,4,5,8,9,11-hexaazabenzophenanthrene-hexacarboxynitrile (HAT-CN), copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(3-methylphenylamino)phenoxybenzene (m-MTDAPB), 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), 4,4',4"-tris(N-(2-naphthyl)-N-phenylamino)triphenylamine (2-TNATA), N4,N4,N4',N4'-tetra([1,1'-biphenyl) [1,1'-biphenyl]-4,4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine), bis(N-(1-naphthyl-n-phenyl))benzidine (α-NPD), N,N'-bis(naphthyl-1-yl)-N,N'-biphenyl-benzidine (NPB) or N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), etc.

[0157] There are no particular restrictions on the compounds contained in the luminescent layer, and either a single luminescent compound or a luminescent host compound can be used, as long as it is commonly used as the luminescent layer compound.

[0158] The luminescent compounds used as the aforementioned luminescent layer include, but are not limited to, compounds that exhibit phosphorescence, fluorescence, thermally activated delayed fluorescence (TADF, also known as E-type delayed fluorescence), triplet-triplet quenching, or a combination of these processes that can induce luminescence. The luminescent compounds can be selected from a variety of materials depending on the desired luminescence color. Non-limiting examples of luminescent compounds include phenanthrene, anthracene, pyrene, tetraphenylene, pentaphenylene, perylene, naphthopyrene, dibenzopyrene, fluorene, and pyroxazole derivatives, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bistyrene derivatives, bistyreneylarylene derivatives, diazabenzodiindacene derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives, dibenzofuran derivatives, coumarin derivatives, dicyanomethylenepyran derivatives, and dicyanomethylenethiazolinone derivatives. Derivatives of uranium, polymethimide, anthocyanin, oxobenzanthracene, xanthones, rhodamine, fluorescein, pyranonium, quinolone, acridine, oxazine, phenoxy, quinacridone, quinazoline, pyrrolopyridine, furanopyridine, 1,2,5-thiadiazolpyrene, pyrrolemethylene, violetone, pyrrolopyrrole, squaric acid cyanine, dibenzothrone, phenazine, acridineone, desoxyflavin, fluorene, benzo[a]fluorene, aromatic boron, aromatic nitrogen-boron, and metal complexes (complexes of metals such as Ir, Pt, Au, Eu, Ru, Re, Ag, Cu, and heterocyclic ligands).Examples include N1,N1,N6,N6-tetrakis(4-(1-methsilyl)phenyl)pyrene-1,6-diamine, 2,12-di-tert-butyl-5,9-bis(4-(tert-butyl)phenyl)-7-(3,5-di-tert-butylphenyl)-5,9-dihydro-5,9-diaza-13b-borona[3,2,1-de]anthracene (t-DABNA-dtB), platinum octaethylporphyrin (PtOEP), and Ir(ppy )3, Ir(ppy)2(acac), Ir(mppy)3, Ir(PPy)2(m-bppy), BtpIr(acac), Ir(btp)2(acac), Ir(2-phq)3, Hex-Ir(phq)3, Ir(fbi)2(acac), FAC-Tris(2-(3-p-xylyl)phenyl)pyridine (III) (fac-Tris(2-(3-p-xylyl)phenyl)pyridine) iridium (III)), Eu(dbm)3(Phen), Ir(piq)3, Ir(piq)2(acac), Ir(Fliq)2(acac), Ir(Flq)2(acac), Ru(dtb-bpy)3·2(PF6), Ir(BT)2(acac), Ir(DMP)3, Ir(M phq)3, Ir(phq)2tpy, fac-Ir(ppy)2Pc, Ir(dp)PQ2, Ir(Dpm)(Piq)2, Hex-Ir(piq)2(acac), Hex-Ir(piq)3, Ir(dmpq)3, Ir(dmpq)2(acac), FPQIrpic and FIrpic, etc.

[0159] As the host compound for the luminescent layer, a luminescent host, a hole transport host, and an electron transport host, or a combination thereof, can be used. Non-limiting examples of luminescent host compounds include fused-ring derivatives such as anthracene and pyrene, bistyrene derivatives such as bis(styrene)-anthracene or styrene-based benzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzo[a]fluorene derivatives, and N... Phenylenecarbazole derivatives (9-phenylcarbazole), carbamate derivatives, etc. Non-limiting examples of main substances for hole transport include carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, triarylamine derivatives, indolecarbazole derivatives, and benzoxazinofexaazine derivatives. Non-limiting examples of main substances for electron transport include pyridine derivatives, triazine derivatives, phosphine oxide derivatives, benzofuranpyridine derivatives, and dibenzoxazolidinium derivatives. Examples include 9,10-bis(2-naphthyl)anthracene (ADN), tris(8-hydroxyquinoline)aluminum (Alq3), Balq (8-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis(2,2-bistyryl)-1,1'-biphenyl) series, spiro-DPVBi (spiro-4,4'-bis(2,2-bistyryl)-1,1'-biphenyl), LiPBO (2-(2-benzoxazolyl))-lithium phenolate), bis(biphenylvinyl)benzene, aluminum-quinoline metal complexes, imidazole, thiazole, oxazole metal complexes, etc.

[0160] There are no particular limitations on the electron injection layer or electron transport layer compound, and any compound can be used as long as it is commonly used as an electron injection layer or electron transport layer compound. Non-limiting examples of electron injection layer or electron transport layer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, pyrene derivatives, coumarin derivatives, naphthimide derivatives, anthraquinone derivatives, biphenylquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives, thiophene derivatives, triazole derivatives, thiadiazole derivatives, metal complexes of hydroxyquinoline derivatives, quinolinol metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzo[a]azole compounds, gallium complexes, pyrazole derivatives, perfluorophenylene derivatives, and triazine derivatives. The materials include pyrazine derivatives, benzoquinoline derivatives, imidazopyridine derivatives, borane derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives, naphthidine derivatives, aldehyde-pyrazine derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, bis(5-phenylene oxide) metal complexes, quinolinol metal complexes, hydroxyazole metal complexes, azomethyl alkaloid metal complexes, tyrosine metal complexes, flavonol metal complexes, benzoquinoline metal complexes, and metal salts. These materials can be used alone, but mixing them with other materials is also acceptable. For example, they can include substances such as 2-(4-(9,10-bis(naphthyl-2-yl))anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazolium, tris(8-hydroxyquinoline)aluminum (Alq3), LiF, Liq, Li2O, BaO, NaCl, and CsF.

[0161] There are no particular restrictions on the compounds used in the electron transport auxiliary layer located between the electron transport layer and the luminescent layer; any compound can be used as long as it is commonly used as an electron transport auxiliary layer compound. For example, the electron transport auxiliary layer can contain pyrimidine derivatives, etc.

[0162] The organic light-emitting diode of one embodiment of the present invention can be either front-emitting or back-emitting.

[0163] An organic light-emitting diode according to an embodiment of the present invention can be used in a display device.

[0164] The organic light-emitting diode of one embodiment of the present invention can be applied to transparent display devices, mobile display devices, flexible display devices, etc., but is not limited thereto.

[0165] An embodiment of the organic light-emitting diode of the present invention may include a tandem structure, the structure including multiple light-emitting stacks between an anode and a cathode.

[0166] The following describes the synthesis method of the above-mentioned compounds through representative examples. However, the synthesis method of the compounds of the present invention is not limited to the methods illustrated below.

[0167] [Synthesis example]: A synthetic example of representative compound 1 is described. Compounds of chemical formula A of the present invention can be synthesized in a similar manner to the reaction of compound 1.

[0168] In the following reaction formulas, as typical examples, the solvent, catalyst, protecting group, leaving group, reaction temperature, and reaction time can all be equivalent to those used.

[0169] 1. Synthesis of Compound 1 Compound 1 can be synthesized in the following manner, but is not limited thereto.

[0170] Reaction 1:

[0171] Under a nitrogen stream, reactant 1 (35 mmol), reactant 2 (36 mmol), Pd2(dba)3 (0.5 mmol), Sphos (1 mmol), t-BuONa (52 mmol), and toluene (150 mL) of compound 1 were placed in a reaction flask, stirred, and refluxed. The organic layer was extracted with toluene and water. The extracted solution was treated with MgSO4 to remove residual water, concentrated under reduced pressure, purified by column chromatography, and recrystallized to obtain the product. The synthesis results of compound 1 are shown in Table 1 below.

[0172] Representative synthesized compounds are shown in Table 1 below, and specific compounds of the present invention and similar compounds can be synthesized by the above-described synthesis examples.

[0173] Table 1

[0174] The effects of the compounds of the present invention were confirmed by the following experiments, which are only typical examples and the experimental examples are not limited thereto.

[0175] Experimental Example 1: Simulation Results of Hole Transport Auxiliary Layer The hole transport auxiliary layer reduces hole accumulation at the emissive layer interface due to the HOMO energy level difference between the hole transport layer and the emissive layer. Therefore, preferably, the HOMO energy level difference with the emissive layer is smaller than the HOMO energy level difference with the hole transport layer. Furthermore, it should have a higher LUMO energy level than the emissive layer to minimize electron leakage from the emissive layer to the hole transport layer.

[0176] To confirm whether the compound represented by chemical formula A of the present invention is suitable as a hole transport auxiliary layer material, the HOMO level (eV) and LUMO level (eV) were calculated using Spartan software (B3LYP DFT 6-31G* by spartan'16), and are shown in Table 2 below.

[0177] Table 2

[0178] Example 1: Fabrication of an organic light-emitting diode (blue light-emitting layer) The substrate, which is layered with ITO (100nm) as the first electrode (anode) of the organic light-emitting diode, is divided into a second electrode (cathode) region, a first electrode (anode) region, and an insulating layer using a photo-lithography process for patterning. Then, UV-ozone treatment and O2:N2 plasma are used to treat the surface to improve the work function of the first electrode (ITO) and to clean it.

[0179] Then, a mixture of 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyrene-2-ylidene)-malonadionitrile (NDP-9) and N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine) was deposited on the anode at a thickness of 10 nm as a hole injection layer (HIL). Next, a hole transport layer (N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine) is formed with a thickness of 100 nm on the hole injection layer above the above hole injection layer. Compound 31 is formed with a thickness of 15 nm on the above hole transport layer (HTL) as a hole transport auxiliary layer.

[0180] Using 9,10-bis(2-naphthyl)anthracene (ADN) as the main component and 2,12-di-tert-butyl-5,9-bis(4-(tert-butyl)phenyl)-7-(3,5-di-tert-butylphenyl)-5,9-dihydro-5,9-diaza-13b-borona[3,2,1-de]anthracene (2,12-Di-tert-butyl-5,9-bis(4-(tert-butyl)...)... A blue luminescent layer with a thickness of 25 nm is deposited on top of the hole transport auxiliary layer using 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (2-(4-(9,10-Di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole and Liq in a 1:1 weight ratio and deposited as an electron transport layer (ETL) with a thickness of 25 nm. An electron injection layer (Liq) with a thickness of 1 nm is deposited on top of the aforementioned electron transport layer (ETL), and a mixture of magnesium and silver in a 1:4 weight ratio is deposited as a cathode with a thickness of 16 nm. On the cathode, N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) is deposited as a capping layer with a thickness of 60 nm. A seal cap containing a desiccant is attached to the capping layer using a UV-curable adhesive to form a protective film (encapsulation layer or protecting layer) to fabricate the organic light-emitting diode (OLED), thereby protecting the OLED from atmospheric oxygen or moisture.

[0181] Examples 2 to 57 Except for replacing the material of compound 31, which was used as the hole transport auxiliary layer material in Example 1 above, with the materials shown in Table 3 below, organic light-emitting diodes of Examples 2 to 57 were prepared in the same manner as in Example 1 above.

[0182] Comparative Examples 1 to 4 Organic light-emitting diodes of Comparative Examples 1 to 4 were prepared using the same method as in Example 1, except that the material of compound 31 used as the hole transport auxiliary layer material in Example 1 was changed to the following compounds: compound A, compound B, compound C, and compound D.

[0183]

[0184] Experiment Example 2: Performance Evaluation of Organic Light Emitting Diodes (Blue Diode) For the organic light-emitting diodes prepared in Examples 1 to 57 and Comparative Examples 1 to 4 above, a 10 mA / cm² pressure was applied using a CS-2000 from Konica Minolta. 2 The driving voltage (V), efficiency (Cd / A), and Y-color coordinates (CIE 1931 standard, CIEy) were measured using the current. Furthermore, using McScience's M6000, at 10mA / cm... 2 The lifetime (LT95) (hrs) was measured by using a constant current drive to confirm the time required for the brightness to decrease from the initial brightness level to 95%. Furthermore, the Blue Index (BI = (Cd / A) / CIEy) value was calculated and recorded using efficiency and color coordinate values. The measurement results are shown in Table 3 below.

[0185] Table 3

[0186] In the case of the organic compound represented by chemical formula A of the present invention, the 4-position of dibenzofuran is replaced by an umbrella-shaped terphenyl group, and an arylamine group is contained at the 1-position. The Ar group contains a heteroaryl group or a fused polycyclic group. As can be confirmed from Table 3, the organic light-emitting diode of the present invention containing the organic compound represented by chemical formula A can not only have excellent color performance, but also ensure characteristics such as low driving voltage, high current efficiency and long life.

[0187] Conversely, Comparative Examples 1 and 2 lack heteroaryl or fused polycyclic aryl groups, and Comparative Examples 3 and 4 have structures in which the substituted terphenyl and amino groups in dibenzofuran are positioned differently from those of the present invention. Device evaluation results confirm that the performance of this device is not superior to that of the compound represented by chemical formula A of the present invention.

[0188] Experimental Example 3: Measurement of the lowest triplet energy (T1) For the compounds of the present invention represented by chemical formula A and comparative example compounds A, B and C, the lowest triplet energy (Triplet 1, referred to as "T1") (unit: eV, absolute value) was calculated by quantum computing experiments using Gaussian software (B3LYP DFT 6-31G* by Gaussian 16), and the results are shown in Table 4 below.

[0189] Table 4

[0190] As shown in Table 4, the organic compound represented by chemical formula A of the present invention can have a suitable range of triplet energy levels (T1) as a hole transport layer or a hole transport auxiliary layer, thereby effectively suppressing the diffusion of triplet excitons generated in the light-emitting layer to the outside and providing luminous efficiency and device lifetime characteristics.

[0191] On the other hand, when the triplet energy level is low, it is impossible to prevent the diffusion of triplet excitons generated in the light-emitting layer, which can reduce the efficiency of the device.

[0192] Although the preferred embodiments of the present invention have been described in detail above, the scope of protection of the present invention is not limited thereto. Various modifications and improvements made by those skilled in the art using the basic concepts of the present invention as defined in the claims are within the scope of protection of the present invention.

Claims

1. An organic compound, represented by the following chemical formula A, characterized in that, Chemical formula A In the above chemical formula A, X above represents oxygen or sulfur. The n1 and n2 mentioned above are integers from 0 to 5. The above n3 is an integer from 0 to 3. The above n4 is an integer from 0 to 2. The above n5 is an integer from 0 to 4. The L1 and L2 groups mentioned above may be the same or different from each other, and each is independently a single-bonded, substituted or unsubstituted aryl group with 6 to 30 carbon atoms. The Ar1 and Ar2 mentioned above may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms. The R1 to R5 mentioned above may be the same as or different from each other, and each independently is selected from one of the following groups consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 60 carbon atoms. When L1, L2, Ar1, Ar2 and R1 to R5 are substituted, the substituents are selected from one or more of the group consisting of deuterium, cyano, nitro, halogen, hydroxyl, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 30 carbon atoms, heteroaryl having 3 to 60 carbon atoms, alkylamino having 1 to 10 carbon atoms, arylamino having 6 to 30 carbon atoms, heteroarylamino having 1 to 30 carbon atoms, alkylsilyl having 1 to 10 carbon atoms, arylsilyl having 6 to 30 carbon atoms, alkoxy having 1 to 10 carbon atoms, aryloxy having 6 to 30 carbon atoms, alkylthio having 1 to 10 carbon atoms, and arylthio having 6 to 30 carbon atoms. When multiple substituents are present, each substituent may be the same or different from the others.

2. The organic compound according to claim 1, characterized in that, The Ar1 mentioned above is selected from the group consisting of substituents represented by M1 to M44 below: in, * indicates a binding site.

3. The compound according to claim 1, characterized in that, The Ar2 mentioned above is selected from the group consisting of substituents represented by A1 to A58 below: in, * indicates a binding site.

4. An organic light-emitting diode, characterized in that, include: First electrode; The second electrode is disposed opposite to the first electrode; and One or more organic layers are located between the first electrode and the second electrode. At least one of the above-mentioned organic layers contains an organic compound represented by chemical formula A according to claim 1.

5. The organic light-emitting diode according to claim 4, characterized in that, An organic layer containing an organic compound represented by the above chemical formula A is a hole transport layer or a hole transport auxiliary layer.

6. A display device, characterized in that, Including the organic light-emitting diode according to claim 4.

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